73591-08-9

Basic information

• Product Name: 3-methoxy-2-phenylacrylonitrile
• Synonyms: 3-methoxy-2-phenylacrylonitrile
• CAS NO: 73591-08-9
• Molecular Weight: 159.188
• Mol File: 73591-08-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-methoxy-2-phenylacrylonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-2-phenylacrylonitrile(73591-08-9)
• EPA Substance Registry System: 3-methoxy-2-phenylacrylonitrile(73591-08-9)

Safety Data

• Hazardous Substances Data: 73591-08-9(Hazardous Substances Data)

Upstream product

• 140-29-4 phenylacetonitrile 
• 22252-92-2 3-hydroxy-2-phenylacrylonitrile 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 21419-05-6 4-amino-5-phenylpyrimidine 
• 77609-05-3 6-amino-2-hydroxy-5-phenyl-nicotinonitrile 
• 1621968-37-3 3-amino-N-(4-methoxyphenyl)-4-phenylthiophene-2-carboxamide 
• 1621966-56-0 3,7-diphenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621967-91-6 3-(4-methoxyphenyl)-2-methyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621967-92-7 3-(4-chlorophenyl)-7-phenylthieno[3,2-d]pyrimidin-2,4(1H,3H)-dione 
• 1621968-41-9 2-chloro-3-(4-chlorophenyl)-7-phenyl-2,3-dihydrothieno[3,2-d]pyrimidin-4(1H)-one 
• 1621967-93-8 3-(4-chlorophenyl)-2-(dimethylamino)-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 82437-64-7 methyl 3-amino-4-phenyl-2-thiophenecarboxylate 
• 1621967-97-2 3-allyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621967-95-0 3-butyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621968-14-6 3-isobutyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621968-15-7 3-neopentyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 
• 1621967-99-4 3-cyclobutyl-7-phenylthieno[3,2-d]pyrimidin-4(3H)-one 

Relevant articles and documents

Synthesis and biological evaluation of N3-alkyl-thienopyrimidin-4-ones as mGluR1 antagonists

Metabotropic glutamate receptor subtype 1 (mGluR1) is a potential target for the treatment of neuropathic pain, and there has been much effort to discover mGluR1 antagonists. In this study, a series of N3-alkyl-thienopyrimidin-4-ones were prepared by introducing various alkyl and aryl groups to the N3- and 7-positions of the thienopyrimidin-4-one core structure, respectively, and their inhibitory activities against mGluR1 were biologically evaluated. Structure-activity relationship study revealed that the trans-4-methylcyclohexyl, cycloheptyl, and cyclooctyl groups at N3-position, and 2-fluorophenyl group at 7-position were most effective in potentiating the inhibitory activity of the thienopyrimidin-4-one derivatives against mGluR1. Among the synthesized compounds, 3-cyclooctyl-7-phenylthienopyrimidin-4-one and 3-cycloheptyl-7-(2-fluorophenyl)thienopyrimidin-4-one exhibited the most potent inhibitory activities with IC50 values of 115 and 107 nM, respectively.

Novel thienopyrimidinones as mGluR1 antagonists

There has been much attention to discover mGluR1 antagonists for treating various central nervous system diseases such as seizures and neuropathic pain. Thienopyrimidinone derivatives were designed, synthesized, and biologically evaluated against mGluR1. Among the synthesized compounds, 3-(4-methoxyphenyl)- 7-(o-tolyl)thienopyrimidin-4-one 30 exhibited the most potent inhibitory activity with an IC50 value of 45 nM and good selectivity over mGluR5. Also, the selective mGluR1 antagonist 30 showed marginal hERG channel activity (IC50 = 9.87 μM), good profiles to CYP isozymes, and a good pharmacokinetic profile. Overall, the compound 30 was identified as a selective mGluR1 antagonist with a good pharmacokinetic profile, which is probably devoid of cardiac side effect and drug-drug interactions. Therefore, the compound 30 can be expected to be broadly used as mGluR1 antagonistic chemical probe in in vitro and in vivo study for investigating CNS diseases.